It's been a while, I know, so a little reminder: in a totally canon-compliant ( but not canon ) way, John's actual last name is Sullivan. You'll see why I point it out again.
MANY HAPPY RETURNS
Harold Finch: "Anyway, I think you've earned some time off. Especially today. Or did you think I didn't know? Happy Birthday."
He's staring, he knows – doesn't matter, after all that's basically his default setting. Birthday... It's not exactly right, and certainly not important. But for so many years, no one bothered wishing him a happy birthday, to the point that he, of all people, had almost forgotten it. Of course, he knows the date of his birth. He hasn't forgotten that, no – he has simply forgotten that to most people, it actually means something. That it used to mean something to him, too.
Harold Finch: "I respect your privacy, John."
Or he pretends to, which wouldn't surprise John. Because if it's possible that now, Finch doesn't monitor him all the time, he doubts it was the case during the first months, back when there wasn't even a layer of trust between them. It's alright. It's better than if the older man simply threw his knowledge in John's face every two minutes.
Mr Han: "As I recall, John, you don't make any move you're not sure of."
It's more that he doesn't make any move without a clear understanding of the risks, of how much it could potentially cost him. But, close enough.
John Reese: "She said she would wait."
John can't ask, won't ask – but for now, all he can think of is that perhaps, Jessica ended her life. That he wasn't there soon enough to stop her from doing it. He has no idea why she would do that, but her words, the last time they spoke...
John Reese: "You were risking his cover by even approaching him."
A marshal, of all people, should know that – never mind that Finch isn't actually a CI, because that's entirely not the point.
Harold Finch: "When I was first building the machine, I kept seeing the same numbers come up – a week, a month, six months apart. Usually women. At first I thought it was a mistake. How could anyone's life be repeatedly threatened? And then I realized... They were living with the person who would eventually kill them."
Was Jessica one of them? It's all he can think about.
John Reese: "Show them what a real monster looks like."
Not to say that these men aren't monsters – they are. But him... He's a worse one. They are the small fry, who prey on the ones who are closest to them – who are the easiest to torture. Real monsters, on the other hand... While some of them also prey on the innocent, their most definite feature is that they aren't afraid to hunt down other monsters.
Harold Finch: "And then maybe you can explain the wisdom of antagonizing an entire law enforcement agency."
Finch is saying this as if he doesn't already have a few of said law enforcement agencies on his back.
John Reese: "Leave the laptop now, Harold. And get out."
He knows that Finch probably has the wrong idea – like for Andrew Benton – but he won't correct him. And he won't let him come. First of all, because if Finch comes with him and tries to talk him out of it, John will probably get irritated, and as a result get more likely to change his mind about Brad Jennings – and not in the way Finch wants. Second, because while he does intend to send Jennings to Mexico, he might very well change his mind once he sees the bastard again.
John Reese: "Finch, you hired me to take care of these things. You don't like how I do it, hire someone else."
He knows, again, that Finch has the wrong idea. But his point still stands, and he doesn't appreciate Finch having decided to sidebench him, thinking he knew best. He didn't. Especially not without past proof of weakness on John's part.
Brad Jennings: "You've never been in love, have you? Really, truly in love?"
Oh yes, he has. Two times, probably. And both times, it ended badly. Both times he walked out, because they deserved better. Both times, he threatened someone to protect the one he loved. None of these times he pursued them like Jennings has done. So, yes, he has been in love. And Jennings will soon be able to discuss it with Peter Arndt, forgotten together in Torreón Penitentiary.
Joss Carter: "This can't end like New Rochelle."
Except Carter doesn't know how New Rochelle ended. She thinks she does. She doesn't – not yet.
John Reese: "That I'll do what needs to be done."
Because if he doesn't, who will? There isn't always a good, legal solution. If there was, he'd still be a cop, not a dubious vigilante with a suspiciously dark past. He's there to take care of what people like Carter can't deal with.
Peter Arndt: "Sullivan sends you?"
Oh, the irony in that question.
John Reese: "Good question. Haven't known the answer for a long time. I know who I was. I was the guy who left her behind. You know why? The real reason? Because I thought she deserved someone better than me. I thought she deserved someone who would look after her... Be there for her. I thought she deserved someone like you. So I don't know. I was hoping you could tell me."
She did. Jessica deserved all that. She deserved someone so much better than him. Except she had apparently gotten worse – no, not really; he still was the bigger monster. But John, at least, would never have threatened her life. So now, he guesses, he is the one who was wrong. The one who allowed her to be killed by his "better" replacement.
John Reese: "See... when you find that one person who connects you to the world... You become someone different... Someone better. When that person is taken from you... What do you become then?"
People don't change, he's sure of that. They always remain in their own potential. But having that one person... It had allowed him to become the better version of himself, the best his potential had to offer. Now, what was he? Now that he didn't have a reason to try and be the best version? Now that she was gone?
Harold Finch: "What I know, Mr. Reese... Is that New Rochelle happened before we started working together. And because of that, there was nothing that either one of us could have done."
That's not an answer, of course. That's Finch not admitting it out loud, that Jessica had been a number. And somehow, that's the most John suspects he can take right now. Because he doesn't think he'd be able to deal with a confirmation – a confirmation that, had he been there sooner, had he already been working for Finch... he may have been able to save Jessica.
